Microsoft Teams is a collaborative communications tool in the same vein as Slack. You get your logical ‘teams’ together, folks chat and collaborate in ‘channels,’ and somehow that open office plan your company loves so much is totally justified because just look at that collaboration in action.

I’m a Slack guy. I like Slack over Teams for a few reasons which will probably become clear as I go through this.

The topic of the day is: CONVERSATIONS.

Teams organizes discussions around “conversations.” A conversation is sort of like the first post in a forum thread. It sets the topic of the conversation and replies on that conversation are attached chronologically to that conversation.

This is interesting to understand because it’s very, very different than Slack or other group chat solutions. In a group chat, messages are generally the first-class object. Slack added “threads” that approximate this conversation concept, but it’s still not the same.

Let’s say you want to search for something that was said six months ago. You remember a few key words and want to see the context.

In Slack, you’ll search, find the message, and when you click it you’ll see the message in chronological context of the rest of the messages. You can scroll up and down to find what you need, follow that thread to the next chronological conversation, or follow it back to see what led to the discussion in the first place.

In Teams, you’ll search, find the message, and when you click it you’ll see the conversation that contains the message. Just that conversation. It may not even pop you to the message itself, depending on if you’re lucky or if Teams is misbehaving. Outside of the conversation, there’s no chronological context. What else was discussed that day? Who’s to say?

Now let’s say you want to reply to a discussion that was being had earlier. You thought of something to add and you want to mention it.

In Slack, you can scroll back in the timeline to find the message. You can start a thread from that, or you can grab some text from it, quote it, and add your info to the main channel. Either way, pretty easy to find the earlier conversation.

In Teams, the timeline is not arranged chronologically. At least, not the way you might think. The timeline is ordered by “most recently replied to” conversation. If someone replies to a conversation, that conversation jumps to the bottom of your timeline as “most recent.” The conversation may have started a year ago, if someone comments on it, it’s suddenly most recent.

This means a couple of things in Teams that aren’t necessarily obvious:

• Search is the only real way to find things. You can’t just scroll back necessarily and see the history.
• You can never say “scroll up about X lines to see what was said” because… “up” isn’t up. The timeline dynamically rearranges on you so as soon as someone responds to that earlier conversation, everything appears in a different order.

What all this yields is that it’s important to know when to continue an existing conversation and when to start a new one.

That’s a really, really hard thing to do because conversation can be organic. However, you sort of have to “run the conversation” the way you “run a meeting” - curbing things that are off topic or getting folks to start new topics.

Why?

Let’s say there’s a conversation someone starts about the weather in Florida. It’s nice, sunny, might rain next week. That conversation goes for a while, talking about weather patterns and seasons. Then you see something like this:

Bob: The sun can really beat down and hit hard.

Alice: The sun is why my favorite season there is Summer.

Bob: It sure means a hot baseball season, though. I can barely get out to games in that heat.

Carl: How are the Marlins doing recently? I saw they traded pitchers.

Bob: They did, and now they’re not doing so well.

Carl: Maybe they should watch that movie Moneyball where they make smarter trades based on stats.

Bob: You could be right. I did see that the Yankees made a good trade this week.

The topic is “weather in Florida” but suddenly has now been totally derailed by a side conversation about baseball.

At first, you might think, “Who cares? It’s not that big of a deal.”

Well, sort of, and sort of not.

Let’s say this is a long conversation. Let’s also say it’s not about inconsequential topics, but about decisions being made for your business.

In six months, you want to go back and find out what was decided. You do a search… and remember how search results show you conversations not messages? You click on the search result and you’re presented with a wall of text where you have to do a manual search to get past all the totally unrelated junk.

This is generally not helped by the fact Teams “conveniently” hides the main body of longer conversations requiring you to click and expand them. Only the last few replies in a conversation are displayed.

It’s a real challenge in Teams when conversations and collaboration become organic like this. Sometimes it’s good to let open-ended discussions flow, and if there’s a conversation started where that’s intentional, great. Some meetings are like that, too. On the other hand, if you have a conversation on “standards for writing documentation” and someone derails it with argumentation about Oxford comma usage and “Hey, I went to Oxford!” and “Oh, really, were you born there or did you go overseas for college?” then things fall apart quickly: Search results become useless, notifications about changes to the conversation become useless, and the timeline rearranges to show the conversation has been updated with off-topic content.

If you’re trying to make the most of your time in a large set of teams and channels, one or two of these isn’t a problem but everyone taking conversations into odd directions makes managing time and discussion very hard.

Finally, it doesn’t help that chats don’t have conversations. If you get into a group chat then it’s like a standard app - it’s chronological, the timeline doesn’t rearrange, etc. It’s different if you’re in team channels. If you’re switching between chats and channels a lot, this can be really jarring.

“Couldn’t you just get everyone to agree to not use the conversations?” The idea here being if everyone used “conversations” as “individual messages” then the problems go away. I’ve tried this, and if you’re only scrolling this works fine. It breaks down if anyone, at any time, forgets and does a reply to a conversation rather than posting a new message. Any reply and the timeline rearranges. It’s done. Further, search won’t work because you can’t see conversations in relation to each other, so all you will ever get in search results is that one message.

All of this is basically why I like Slack far, far better. The organic conversation flows better, you can start threads if you want but you don’t have to, search works… it’s generally better for how I work.